US2865917A - Merocyanine dyes - Google Patents

Merocyanine dyes Download PDF

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Publication number
US2865917A
US2865917A US676383A US67638357A US2865917A US 2865917 A US2865917 A US 2865917A US 676383 A US676383 A US 676383A US 67638357 A US67638357 A US 67638357A US 2865917 A US2865917 A US 2865917A
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US
United States
Prior art keywords
methyl
ethanol
benzoyl
thiohydantoin
phenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US676383A
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English (en)
Inventor
Fry Douglas James
Lea Bernard Alan
Kendall John David
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Ilford Imaging UK Ltd
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Ilford Ltd
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Publication date
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Publication of US2865917A publication Critical patent/US2865917A/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes
    • G03C1/22—Methine and polymethine dyes with an even number of CH groups

Definitions

  • This invention relates to merocyanine dyes, their production and use.
  • alkoxy these are preferably lower alkoxy or ethoxy.
  • D may be the residue of any five-membered or sixmembered heterocyclic ring system including thiazoles, oxazoles, selenazoles and their polycyclic homologues groups are referred to groups, e. g. methoxy l COR; XI
  • the merocyanine dyes are valuable. optical sensitisers for silver halide photographic emulsions, and the invention emulsions (and photographic elements containing the same) which contain such dyes in sensitising amount.
  • the sensitivity was extended to 6450 A. with a maximum at 6200 A, whilst in a silver chlorobromide the sensitivity extended to 6400' A. with a maximum. at 5900 A,
  • EXAMPLE 4 3-benzoyl-1-phenyZ-Z-thio-S-f (3-ethyl-2 :3-dihydro-2- benzoxazolylidene ethylidenel thiohydantojn
  • the compound was prepared as in Example 1, but starting with Z-methyl benzoxazole etho-p-toluene sulphonate
  • the crude dye (1.9 gm.) crystallised from a mixture of ethanol (400 ml.) and chloroform (60 mls.) as purple needles (0.8 gm.) with M. Pt. 290-292 C.
  • the sensitivity When incorporated in a silver iodobromide emulsion the sensitivity was extended to 6000 A. with a maximum at 5850 A., whilst in a silver chlorobrornide the sensitivity extended to 5850 A. with a maximum at 5500 A.
  • EXAMPLE 5 3-benz0yl-I-phenyl-2-thi0-5-[ (3-melhyl-2-thiazolidinylidene) ethylidene] thiohydantoin
  • the compound was prepared in the same way as Example 1 except that the starting material was Z-methylthiazoline metho-p-toluene sulphonate (2.9 gm.), and the dye condensation carried out in mls. of ethanol.
  • the crude dye (1.3 gm., M. Pt. 245249 C.) was boiled with ethanol (250 ml.) and the residue crystallised from chloroform (75 ml.) from which the product separated as a red powder (0.45 gm.) with M. Pt. 265-268 C.
  • the sensitivity was extended to 5650 A. with a maximum at 5300 A.
  • EXAMPLE 6 3-benz0yl-1-phenyl-2-thio-5 (3-ethyI-Z-thiazolidinylidene) ethylidene] thiohydantoin
  • the compound was prepared in the same way as Example 1, except that the starting material was 2-methylthiazoline etho-p-toluene sulphonate and the dye condensation carried out in 10 mls. of ethanol.
  • the crude dye (1.2 gm.) was dissolved in a mixture of ethanol (200 mls.) and chloroform (30 mls.) from which the product separated as red crystals (0.9 gm.) with M. Pt. 247249 C.
  • the sensitivity was extended to 5650 A. with a maximum at 5250 A.
  • EXAMPLE 7 3-benz0yl-1 -phenyl-2-thio-5 [(1 :4 :4-trimethyl-2-pyrrolidinylidene) ethylidene] zhiohydantoin 3-benzoyl-l-phenyl-2-thiohydantoin (2.0 gm.), 2(acetanilinovinyl)-4:4-dimethyl pyrroline methiodide (2.0 gm.), ethanol (10 ml.) and triethylamine (1.4 ml.) were mixed and heated under reflux for 10 minutes. The product which separated on cooling was filtered off and washed with water followed by ethanol. The crude dye (0.7 gm.) had M. Pt. 210214 C. and after two crystallisations from ethanol was obtained as orange-red crystals (0.4 gm.) with M. Pt. 237-239 C.
  • EXAMPLE 8 3-ben z0yl-1-phenyl-2-thio-5 (1-ethyl-4 4-dimLethyl-2- pyrrolidinylidene) ethylia ene] 1h iohydantoin
  • the compound was prepared as in Example 7 except that 2(aeetanilinovinyl)-4:4-dim ⁇ ethyl pyrroline eithiodide (2.1 gm.) was used in place of the methiodide.
  • the crude dye (1.0 gm.) had M. Pt. 245-248 C. and after crystallising from a mixture of ethanol ml.) and chloroform (30 ml.) was obtained as gleaming orange plates (0.65 gm.) with M. Pt. 246-248 C.
  • EXAMPLE l6 3-benzoyl-1-methyl-5 (3-methyl-2:3-dihydr0-2-benzthiazolylidene) butenylidene]-2-thiohydanl0in fl-Anilino-acrolein anil hydrochloride (3.0 gm.), 3- benzoyl-l-methyl-2-thiohydantoin, doubly fused sodium acetate (0.8 gm.) and acetic anhydride (5 ml.) were mixed and heated over a small flame for 3 minutes.
  • R is selected from the class consisting of methyl and ethyl groups
  • D is a residue selected from the class consisting of benzthiazole, benzoxazole and thiazoline nuclei.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Coloring (AREA)
US676383A 1956-08-17 1957-08-05 Merocyanine dyes Expired - Lifetime US2865917A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB25212/56A GB829790A (en) 1956-08-17 1956-08-17 Improvements in or relating to merocyanine dyes

Publications (1)

Publication Number Publication Date
US2865917A true US2865917A (en) 1958-12-23

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Family Applications (1)

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US676383A Expired - Lifetime US2865917A (en) 1956-08-17 1957-08-05 Merocyanine dyes

Country Status (4)

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US (1) US2865917A (en(2012))
DE (1) DE1150771B (en(2012))
GB (1) GB829790A (en(2012))
NL (2) NL219960A (en(2012))

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5482814A (en) * 1993-07-15 1996-01-09 Canon Kabushiki Kaisha Thermal developing photosensitive member and image forming method using the thermal developing photosensitive member

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2177403A (en) * 1935-11-15 1939-10-24 Eastman Kodak Co Dye from imidazolones
US2719152A (en) * 1953-08-03 1955-09-27 Eastman Kodak Co Merocyanine dyes containing a 2-thiohydantoin nucleus and preparation thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2177403A (en) * 1935-11-15 1939-10-24 Eastman Kodak Co Dye from imidazolones
US2719152A (en) * 1953-08-03 1955-09-27 Eastman Kodak Co Merocyanine dyes containing a 2-thiohydantoin nucleus and preparation thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5482814A (en) * 1993-07-15 1996-01-09 Canon Kabushiki Kaisha Thermal developing photosensitive member and image forming method using the thermal developing photosensitive member

Also Published As

Publication number Publication date
NL219960A (en(2012))
DE1150771B (de) 1963-06-27
NL95239C (en(2012))
GB829790A (en) 1960-03-09

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